Streetwise is not a derogatory term:
- North American English also street-smart (informal)
- having the knowledge and experience that is needed to deal with the difficulties and dangers of life in a big city.
- Kids seem much more streetwise these days.
(OLD)
- Having the necessary knack, personality and instinct for survivgal in rough, urban environments.
- Like all serial killers, he had the ability to sense vulnerability among potential victims; he didn't take the streetwise girls, he was after the younger women. (Ann Rule speaking about Gary Ridgway.)
- Possessing a style that embodies the life and microculture located within urban settings, typically in the States.
- You could tell from the way he spat old Tupac lyrics, loitering in the corner with his homies, flipping that Yankees cap on his head like he couldn't give a damn that he was streetwise enough to melt Will Smith.
(Wiktionary)